Literature DB >> 16262378

A proposal for the mechanism-of-action of diazoparaquinone natural products.

Ken S Feldman1, Kyle J Eastman.   

Abstract

Treatment of the representative diazoparaquinone prekinamycin dimethyl ether with Bu3SnH/AIBN in aromatic solvents furnishes moderate-to-good yields of formal aryl adducts wherein a molecule of solvent is attached to the carbon (C(11)) previously bearing the diazo function. Substituent studies provide evidence in support of a radical aromatic substitution mechanism, in which radical addition to the diazoparaquinone function generates an intermediate C(11) vinylic radical.

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Year:  2005        PMID： 16262378      PMCID： PMC2789421          DOI： 10.1021/ja053880w

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  11 in total

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2.  Absolute Rate Constant for the Reaction of Aryl Radicals with Tri-n-butyltin Hydride(1).

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Journal:  J Org Chem       Date:  1996-01-26       Impact factor: 4.354

3.  The mechanism of Bu3SnH-mediated homolytic aromatic substitution.

Authors:  Athelstan L J Beckwith; Vincent W Bowry; W Russell Bowman; Emma Mann; Jonathan Parr; John M D Storey
Journal:  Angew Chem Int Ed Engl       Date:  2004-01       Impact factor: 15.336

4.  Bioactivation as a model for drug design bioreductive alkylation.

Authors:  H W Moore
Journal:  Science       Date:  1977-08-05       Impact factor: 47.728

Review 5.  A survey of natural products which abstract hydrogen atoms from nucleic acids.

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Journal:  Nat Prod Rep       Date:  1993-12       Impact factor: 13.423

6.  Drug uptake and cellular targets of hydroxymethylacylfulvene (HMAF).

Authors:  M C Herzig; B Arnett; J R MacDonald; J M Woynarowski
Journal:  Biochem Pharmacol       Date:  1999-07-15       Impact factor: 5.858

7.  Effects on DNA integrity and apoptosis induction by a novel antitumor sesquiterpene drug, 6-hydroxymethylacylfulvene (HMAF, MGI 114).

Authors:  J M Woynarowski; C Napier; S K Koester; S F Chen; D Troyer; W Chapman; J R MacDonald
Journal:  Biochem Pharmacol       Date:  1997-12-01       Impact factor: 5.858

Review 8.  Discovery and development of sesquiterpenoid derived hydroxymethylacylfulvene: a new anticancer drug.

Authors:  T C McMorris
Journal:  Bioorg Med Chem       Date:  1999-05       Impact factor: 3.641

9.  Diazo group electrophilicity in kinamycins and lomaiviticin A: potential insights into the molecular mechanism of antibacterial and antitumor activity.

Authors:  Radoslaw S Laufer; Gary I Dmitrienko
Journal:  J Am Chem Soc       Date:  2002-03-06       Impact factor: 15.419

10.  Mechanism of Formation of Novel Covalent Drug·DNA Interstrand Cross-Links and Monoadducts by Enediyne Antitumor Antibiotics

Authors: 
Journal:  Biochemistry       Date:  1997-12-02       Impact factor: 3.162
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  6 in total

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Authors:  Hong Geun Lee; Jae Young Ahn; Amy S Lee; Matthew D Shair
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3.  Analysis of diazofluorene DNA binding and damaging activity: DNA cleavage by a synthetic monomeric diazofluorene.

Authors:  Christina M Woo; Nihar Ranjan; Dev P Arya; Seth B Herzon
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-09       Impact factor: 15.336

4.  Development of enantioselective synthetic routes to (-)-kinamycin F and (-)-lomaiviticin aglycon.

Authors:  Christina M Woo; Shivajirao L Gholap; Liang Lu; Miho Kaneko; Zhenwu Li; P C Ravikumar; Seth B Herzon
Journal:  J Am Chem Soc       Date:  2012-10-03       Impact factor: 15.419

5.  Mechanism of the cytotoxicity of the diazoparaquinone antitumor antibiotic kinamycin F.

Authors:  Kimberley A O'Hara; Xing Wu; Daywin Patel; Hong Liang; Jack C Yalowich; Nan Chen; Valerie Goodfellow; Otunola Adedayo; Gary I Dmitrienko; Brian B Hasinoff
Journal:  Free Radic Biol Med       Date:  2007-07-13       Impact factor: 7.376

6.  The cytotoxicity of (-)-lomaiviticin A arises from induction of double-strand breaks in DNA.

Authors:  Laureen C Colis; Christina M Woo; Denise C Hegan; Zhenwu Li; Peter M Glazer; Seth B Herzon
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  6 in total

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